Patent GB-362971-A (GB)
Title: Production of derivatives of oxidised oils or fatty acids, and sulphonated products therefrom
IPC: C11C3/00
Filed: 1930-09-10
Abstract: Oils derived from fatty acids containing at least two olefinic linkages or the fatty acids themselves are treated in the presence of glacial acetic acid with a regulated proportion of hydrogen peroxide under suitable conditions such that some but not all of the unsaturated carbon linkages become saturated by the addition of hydroxyl groups, a portion of the added hydroxy groups becoming acetylated.  The products so obtained may be further treated with sulphuric acid or other known sulphonating agent with or without p previous further acylation by treatment with the appropriate acid anhydride or halide.  The sulphonation may be effected in the presence of known auxiliary agents such as acid anhydrides or pyridine.  Oils to which the invention may be applied include fish oils, tung oil, and linseed oil.  Fatty acids such as may be obtained by the saponification of these oils, for example clupadonic acid and elaeostearic acid, may also be employed singly or as mixtures. According to examples (1) Japanese fish oil is mixed with glacial acetic acid and hydrogen peroxide, and the mixture is heated at 95 DEG  C. for 4 hours.  The oil is separated by decantation or distillation and washed with water until free from acid; (2) the mixture obtained in example (1) after heating for 4 hours at 90 DEG C. is boiled until water distils off.  The boiling is continued under reflux for two hours, and the excess of acetic acid is then removed by distillation.  The oily residue is treated with oleum at 17-20 DEG C. until a sample dissolves in water, then poured into cold water, the oil being separated and neutralized; (3) linseed oil is treated in a similar manner to the fish oil in example (1); and (4) the product is then further treated as in example (2) except that acetic anhydride is added before the addition of oleum.ALSO:Oils derived from fatty acids containing at least two olefinic linkages or the fatty acids themselves are treated in the presence of glacial acetic acid with a regulated proportion of hydrogen peroxide under suitable conditions such that some but not all of the unsaturated carbon linkages become saturated by the addition of hydroxyl groups, a portion of the added hydroxyl groups becoming acetylated.  The products so obtained may be further treated with sulphuric acid or other known sulphonating agent with or without previous further acylation by treatment with the appropriate acid anhydride or halide. The sulphonation may be effected in the presence of known auxiliary agents such as acid anhydrides or pyridine.  Oils to which the invention may be applied include fish oils, tung oil, and linseed oil.  Fatty acids such as may be obtained by the saponification of these oils, for example, clupadonic acid and elaeostearic acid, may also be employed singly or as mixtures.  According to examples (1) Japanese fish oil is mixed with glacial acetic acid and hydrogen peroxide, and the mixture is heated at 95 DEG  C. for 4 hours.  The oil is separated by decantation or distillation and washed with water until free from acid; (2) the mixture obtained in example (1) after heating for 4 hours at 95 DEG  C. is boiled until water distils off. The boiling is continued under reflux for two hours, and the excess of acetic acid is then removed by distillation. The oily residue is treated with oleum at 17-20 DEG  C. until a sample dissolves in water, then poured into cold water, the oil being separated and neutralized; (3) linseed oil is treated in a similar manner to the fish oil in example (1), and (4) the product is then further treated as in example (2), except that acetic anhydride is added before the addition of oleum.